Water → Methyl 2-methylquinoline-7-carboxylate

HRID 338860Notes

Reaction equation

HRID 338860 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[N:3]=1.[C:15]([O-])([O-])=O.[K+].[K+].CI.O>CC(N(C)C)=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 109762212-methylquinoline-7-carboxylic Acid

Product 1

HCID 67978375Methyl 2-methylquinoline-7-carboxylateYield 92.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-methylquinoline-7-carboxylic acid (1.00 g, 5.34 mmol) and K2CO3 (2.36 g, 17.1 mmol) in DMA (10 mL) was added MeI (0.35 mL, 5.61 mmol) dropwise at ambient temperature. The reaction was stirred at ambient temperature for 18 hours. Water (30 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with water and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:5 hexane/ethyl acetate) to give methyl 2-methylquinoline-7-carboxylate (0.99 g, 92.1%) as a solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (1:5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fab3ca08778744dba30ed0482e811524
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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